Here is the full list of all 27 Orwell: Keeping an Eye On You achievements. It takes around 8-10 hours to unlock all of the achievements on Windows.
Make Thought crimes.
Complete Episode Five.
Choose the simple answer.
Reunite a couple.
Complete Episode Four.
Pick up what was left behind.
Don't bother the law.
Complete Episode Three.
Repay the debt.
Complete Episode Two.
Allow catastrophe.
Know all favorites.
Complete Episode One.
Show the rebellious side.
Show the peaceful side.
See no crime in buying a bottle.
Avert catastrophe.
Don't read minds.
Administer justice.
Forgive a crime.
Keep quiet about the intention.
Make an unlawful arrest.
Win the war.
Uncover the truth.
Find out who is there.
End a career.
Set Thought free.